Cyclic Thioether Compound, Vegetable Oil Composition Containing the Same, Their Preparation and Application Thereof

Patent metadata

Field	Value
Publication number	US-2023141112-A1
Application number	US-202117904726-A
Country	US
Kind code	A1
Filing date	Jan 28, 2021
Priority date	Jan 28, 2021
Publication date	May 11, 2023
Grant date	—

Abstract

A cyclic thioether compound has a structure represented by the following formula (I). A vegetable oil composition contains the cyclic thioether compound. When the cyclic thioether compound is used as a drilling fluid lubricant in a drilling fluid. The lubrication performance of the drilling fluid can be significantly improved.

First claim

1 . A cyclic thioether compound, having a structure represented by the following formula (I):

wherein in the formula (I), R 1 is selected from optionally substituted C1-20, C2-10, C4-8 or C6-7 linear or branched hydrocarbyl groups (such as optionally substituted C1-20, C2-10, C4-8 or C6-7 linear or branched alkyl groups, optionally substituted C2-20, C2-10, C4-8 or C6-7 linear or branched alkenyl groups, or optionally substituted C2-20, C2-10, C4-8 or C6-7 linear or branched alkynyl groups), R 2 is selected from single bond and optionally substituted C1-20, C2-10, C4-8 or C6-7 linear or branched hydrocarbylene groups (such as optionally substituted C1-20, C2-10, C4-8 or C6-7 linear or branched alkylene groups, optionally substituted C2-20, C2-10, C4-8 or C6-7 linear or branched alkenylene groups, or optionally substituted C2-20, C2-10, C4-8 or C6-7 linear or branched alkynylene groups), and the sum of the numbers of carbon atoms of R 1 and R 2 is 3 or more (preferably 3-35, more preferably 5-25 or 11-13).

2 . The cyclic thioether compound according to claim 1 , having a structure represented by the following formula (I-1):

wherein in the formula (I-1), X represents O or NR′, R′ is selected from hydrogen and optionally substituted C1-10 linear or branched alkyl groups (preferably from hydrogen and optionally substituted C1-6 or C2-4 linear or branched alkyl groups), Y represents a monovalent end group (preferably selected from hydrogen, and optionally interrupted and optionally substituted C1-10000 linear or branched alkyl groups, more preferably from hydrogen, and optionally interrupted and optionally substituted C1-6 or C2-4 linear or branched alkyl groups, or Y represents a polyether group having a polymerization degree of 1-5000 (preferably 1-500)).

3 . The cyclic thioether compound according to claim 1 , having a structure represented by the following formula (I-2):

wherein in the formula (I-2), each R 3 , being the same or different from each other, is independently selected from optionally substituted C1-39, C9-23, C11-21 or C15-19 linear or branched hydrocarbyl group (such as optionally substituted C1-39, C9-23, C11-21 or C15-19 linear or branched alkyl groups, optionally substituted C3-39, C9-23, C11-21 or C15-19 linear or branched alkenyl groups, or optionally substituted C3-39, C9-23, C11-21 or C15-19 linear or branched alkynyl groups), m is an integer of 1 or more (preferably 1, 2, 3, 4, 5 or 6), n is an integer of 0 or more (preferably 0, 1, 2, 3, 4 or 5), and m+n is an integer of 1 to 10, or 1 to 6 (such as 1, 2, 3, 4, 5 or 6), each X, being the same or different from each other, is independently selected from 0 and NR′, R′ is selected from hydrogen and optionally substituted C1-10 linear or branched alkyl groups (preferably from hydrogen and optionally substituted C1-6 or C2-4 linear or branched alkyl groups), Y 1 represents an optionally interrupted and optionally substituted m+n valent C2-10000 linear or branched alkyl group (preferably an optionally interrupted and optionally substituted m+n valent C2-6 or C2-4 linear or branched alkyl group, more preferably a 1,2,3-trivalent propyl group, or Y 1 represents an m+n valent polyether group having a polymerization degree of between 1 and 5000 (preferably between 1 and 500).

4 . The cyclic thioether compound according to claim 1 , wherein the compound is at least one selected from the group consisting of compounds represented by the following formulae and isomers thereof:

wherein in these formulae, m is an integer of 1 or more (preferably 1, 2, 3, 4, 5 or 6), n is an integer of 0 or more (preferably 0, 1, 2, 3, 4 or 5), and m+n is an integer of 1 to 10, or 1 to 6 (such as 1, 2, 3, 4, 5 or 6), and when m+n=3, Y 1 is a 1,2,3-trivalent propyl group, or when m=1 and n=0, Y 1 is an optionally interrupted and optionally substituted C2-10000 (preferably C2-6 or C2-4) linear or branched alkyl group or a polyether group having a polymerization degree of between 1 and 5000 (preferably between 1 and 500), each Z, being the same or different from each other, is independently selected from hydrogen, oleoyl group, linoleoyl group and stearoyl group, Ra and Rb, being the same or different from each other, are each independently selected from hydrogen and hydroxyl substituted C1-10 linear or branched alkyl groups (preferably from hydrogen and hydroxyl substituted C1-6 or C2-4 linear or branched alkyl groups, more preferably from hydrogen and hydroxyethyl group).

5 . A method for producing a cyclic thioether compound, comprising the steps of:
subjecting an unsaturated fatty acid starting material to a sulfurization reaction in the presence of sulfur (such as elemental sulfur), a benzothiazole-based sulfurization accelerator, an inorganic zinc compound and optionally a long-chain fatty acid, to convert at least one carbon-carbon double bond of the unsaturated fatty acid starting material to a cyclic thioether moiety to obtain the cyclic thioether compound or a product mixture comprising the cyclic thioether compound, wherein the at least one carbon-carbon double bond is non-conjugated double bond.

6 . The method according to claim 5 , wherein the unsaturated fatty acid starting material is at least one selected from the group consisting of optionally substituted C8-40 (preferably C10-24, C16-20 or C18) unsaturated fatty acid (hereinafter referred to as “unsaturated fatty acid” for short), derivatives of the unsaturated fatty acid (hereinafter, the unsaturated fatty acid and the derivative of the unsaturated fatty acid are collectively referred to as “unsaturated fatty acid compound”), and biomass materials (preferably vegetable oils) comprising the unsaturated fatty acid compound, preferably at least one selected from the group consisting of derivatives of the unsaturated fatty acid and vegetable oils comprising a derivative of the unsaturated fatty acid, and/or the vegetable oil is at least one selected from the group consisting of soybean oil, peanut oil, rapeseed oil, camellia seed oil and corn oil.

7 . The method according to claim 6 , wherein the weight ratio of the sulfur:the benzothiazole-based sulfurization accelerator:the inorganic zinc compound:the unsaturated fatty acid compound (particularly the derivative of the unsaturated fatty acid):the long-chain fatty acid is 0.5-12:0.5-16:0.1-8:60-98:0-12, preferably 1-10:0.5-5:0.1-5:75-98:0-10 or 1-6:0.7-7.8:0.3-1.2:79-95.6:2.4-6, and/or, the weight ratio of the sulfur:the benzothiazole-based sulfurization accelerator:the inorganic zinc compound:the biomass material (particularly the vegetable oil):the long-chain fatty acid is 0.5-12:0.5-16:0.1-8:60-98:0-12, preferably 1-10:0.5-5:0.1-5:75-98:0-10 or 1-6:0.7-7.8:0.3-1.2:79-95.6:2.4-6.

8 . The method according to claim 6 , wherein the derivative of the unsaturated fatty acid is at least one selected from the group consisting of anhydride of the unsaturated fatty acid, amide of the unsaturated fatty acid (such as monoamide, diamide, triamide and the like produced from the unsaturated fatty acid and a compound having one or more primary and/or secondary amino groups per molecule) and ester of the unsaturated fatty acid (such as monoester, diester, triester and the like produced from the unsaturated fat

Assignees

• China Petroleum & Chem Corp
• Sinopec Oilfield Service Corp
• Sinopec Shengli Petroleum Eng Co Ltd
• Drilling Tech Research Institute Of Sinopec Shengli Petroleum Engineering Co Ltd

Inventors

• Li Gongrang
• Li Wenbo
• Wang Chengjun
• Sun Bingxiang
• Tian Hui
• Li Ke
• Jia Jianghong
• Wang Xudong
• Yu Lei
• Wang Jun
• Wang Wei
• Li Lei

Classifications

• C07D331/04 Primary

  Four-membered rings · CPC title

• C09K8/035

  Organic additives · CPC title

• C07D277/74

  Sulfur atoms substituted by carbon atoms · CPC title

• C10M135/36

  the ring containing sulfur and carbon with nitrogen or oxygen · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title